Ethanol → HCID 178510427, compound

HRID 1190173Notes

Reaction equation

HRID 1190173 reaction equation
C([O:5][C:6](=[O:39])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[N:19](COCC[Si](C)(C)C)[CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[C:11]([C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.CCO>C(Cl)Cl>[C:23]([C:21]1[N:22]=[C:18]([C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([CH:8]=[CH:7][C:6]([OH:39])=[O:5])=[CH:10][C:11]=2[C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)=[O:17])[NH:19][CH:20]=1)#[N:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 69007915HCID 69007915, compound

Product 1

HCID 178510427HCID 178510427, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-acrylic acid tert-butyl ester (30 mg, 0.055 mmol)(as prepared in the previous step) in 1.0 mL of DCM was added 0.30 mL of TFA, 0.026 mL of EtOH and stirred at RT for 2 h. The mixture was concentrated and the residue triturated with MeOH to give 19 mg (95%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ 14.39 (br s, 1H), 9.83 (s, 1H), 8.38 (d, J=2.5 Hz, 1H), 8.15 (d, J=8.5 Hz, 1H), 7.65 (dd, J=8.5, 1.9 Hz, 1H), 7.57 (d, J=1.9 Hz, 1H), 7.56 (d, J=16.0 Hz, 1H), 6.53 (d, J=16.0 Hz, 1H), 5.83 (m, 1H), 2.31-2.14 (m, 4H), 1.81-1.65 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C20H18N4O3, 363.1 (M+H). found 363.0.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue triturated with MeOH

Sources & evidence

ORD record
ord-e82f84dad03a48778f58429e952c1782
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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